Private charter between Boston and Chicago starts at US$21,500 aboard a light jet.
Private jet charter from Boston (BOS) to Chicago (ORD), and from Chicago (ORD) back to Boston (BOS).
The straight-line distance between Boston and Chicago is about 1,391 km (864 miles), or 751 nautical miles.
From US$21,500 · Reply within the hour · No obligation
Guide pricing for Boston–Chicago spans US$21,500 – US$59,000: from a light jet (Cessna Citation CJ3+) at the entry level to a super midsize jet (Challenger 350) at the top. All cabins are pet-friendly — travel with dogs and pets beside you.
The popular choice for this distance — strong value and cabin comfort. 6-8 seats and 3,700 km of range make it a dependable fit here.
A stand-up cabin and more baggage room for medium-haul comfort. It seats 7-9 and is a frequent choice on sectors of this length.
Intercontinental comfort with a full stand-up cabin and separate sleeping area. 9-12 seats and 5,926 km of range make it a dependable fit here.
| Category | Outbound | Return (±10% wind) | From (USD) | Seats |
|---|---|---|---|---|
| Light Jet · rec. | 2h 11m | 1h 58m – 2h 24m | US$21,500 | 6-8 |
| Midsize Jet | 2h 08m | 1h 55m – 2h 21m | US$30,500 | 7-9 |
| Super Midsize Jet | 2h 00m | 1h 48m – 2h 12m | US$42,000 | 9-12 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Cessna Citation CJ3+ | 2h 11m | US$21,500 – US$30,000 | 6-8 |
| Embraer Phenom 300E | 2h 07m | US$23,500 – US$33,000 | 6-8 |
| Learjet 75 Liberty | 2h 01m | US$26,000 – US$36,000 | 6-8 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Cessna Citation XLS+ | 2h 08m | US$30,500 – US$42,500 | 7-9 |
| Hawker 900XP | 2h 07m | US$33,500 – US$47,000 | 7-9 |
| Embraer Praetor 500 | 2h 02m | US$36,500 – US$51,000 | 8-10 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Challenger 350 | 2h 00m | US$42,000 – US$59,000 | 9-12 |
| Cessna Citation Longitude | 2h 00m | US$46,000 – US$65,000 | 9-12 |
| Embraer Praetor 600 | 2h 02m | US$50,500 – US$71,000 | 9-12 |
Same aircraft, same route — return pricing is symmetric; flight times can vary about ±10% with wind direction.
Guide prices are one-way estimates incl. positioning; taxes/handling extra. Round-trip and one-way both available.
Charter pricing on Boston–Chicago moves with route distance, winds, fuel costs at both ends, and airport charges at origin and destination. We lock in a firm, all-in figure once we match your dates to available aircraft.
Both cities are served by several airports, giving flexibility on slots and routing:
Boston, United States: Boston Logan International Airport.
Chicago, United States: Chicago O'Hare International Airport, Chicago Midway International Airport and Lansing Municipal Airport.
Pick your slot and depart. Private charter between Boston and Chicago is built around your itinerary.
The 2h 11m airborne is uninterrupted time — work, rest, or simply arrive ready.
Private jets access far more airports than commercial flights — reducing transfers and getting you closer to where you need to be.
Guide pricing on Boston–Chicago is published clearly: US$21,500 – US$59,000. Your confirmed quote is all-in.
Boston–Chicago is a frequently chartered domestic sector for executives and families alike, prized for flexibility and time saved.
Budget US$21,500 – US$59,000 one-way depending on aircraft; a light jet sits at the entry point. We confirm a firm figure against live availability.
Roughly 2h 11m airborne across the 1,391 km sector — timings shift a little with winds and aircraft.
Light Jet, Midsize Jet, Super Midsize Jet are the usual choices here; our pick is a light jet for value and comfort on this distance.
Yes — we handle last-minute Boston–Chicago charters, often with as little as 4 hours' notice, subject to aircraft and crew availability.
Absolutely — pets travel in the cabin with you on this route; just tell us the details when you ask for a quote.
Of course: Chicago to Boston runs on the same aircraft and pricing, so round trips are straightforward.
Other flights from Boston | Chicago | United States | North America
